Compare Vacation Rentals & Airbnb in Oakville

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Oakville vacation rentals
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871 Rentals and Airbnb in Oakville

Best family friendly Oakville vacation rentals

Among the 871 accommodations in Oakville, here are the 4 best family friendly rentals

Comfy Condo, Can Sleep 5, Close To Stores, Park - Oakville
9.7 22 reviews

Comfy Condo, Can Sleep 5, Close To Stores, Park

apartment, Toronto
This Toronto apartment rental offers a peaceful, central location, though precise distances to specific landmarks remain unspecified.
The two-bedroom, one-bathroom flat sleeps four guests and includes a kitchen with fridge, freezer, microwave, and dishwasher, plus air conditioning, garden, and parking.
Spacious Basement In Oakville - Oakville
9.9 114 reviews

Spacious Basement In Oakville

apartment, Toronto
This two-bedroom, one-bathroom apartment in Oakville, Ontario, is situated near Oakville Place shopping centre, offering easy access to public transport including a train station and local bus services.
The 4-guest property boasts a fully equipped kitchen with stainless steel appliances, a modern bathroom, and is close to recreational facilities such as bowling alleys, cinemas, nature trails, and various restaurants.
Luxury Walkout Basement Apartment In Oakville - Oakville
9.7 31 reviews

Luxury Walkout Basement Apartment In Oakville

apartment, Milton
This Oakville basement flat, a short drive (approximately 8km) from Milton town centre, offers a peaceful retreat with serene park views.
The self-contained one-bedroom property sleeps four, boasting a high-end kitchen, massage chair, and access to a fitness centre, all within easy reach of local eateries and walking trails.
Cozy 2 Bedroom Basement Apart - Oakville
10 6 reviews

Cozy 2 Bedroom Basement Apart

apartment, Toronto
This two-bedroom Toronto apartment, perfect for group trips of up to four guests, is situated in an unspecified area of the city; further details regarding proximity to specific Toronto landmarks such as the CN Tower or the Royal Ontario Museum are needed.
The 1-bathroom flat features a fully equipped kitchen including a fridge, freezer, and dishwasher, air conditioning, parking, and internet access; additional information on the property's size, interior design, and nearby activities is required for a complete description.

Best Oakville vacation rentals with parking

Modern Luxury Townhome With 2br Balcony Plus Parking - Happy Oaks - Oakville
10 2 reviews

Modern Luxury Townhome With 2br Balcony Plus Parking - Happy Oaks

house, Toronto
This modern luxe residence is situated in Oakville, 26 kilometres from the Mississauga Convention Centre and 32-35 kilometres from Toronto landmarks such as BMO Field, Rogers Centre, and the CN Tower, with Toronto Pearson International Airport located 26 kilometres away.
This property offers free WiFi, private parking, air conditioning, a kitchen, and a balcony, accommodating up to seven guests with a check-out time of 11:00 AM.
Spacious And Luxurious 2br Suite With Huge Windows - Oakville
8.7 3 reviews

Spacious And Luxurious 2br Suite With Huge Windows

apartment, Toronto
This Mississauga apartment, situated 19 kilometres from Toronto's downtown attractions including the BMO Field and Exhibition Place, offers convenient access to both the city and Pearson International Airport (18 kilometres).
This two-bedroom, two-bathroom flat boasts 46 square metres of space, comfortably accommodating up to nine guests and featuring free parking, Wi-Fi, and a fully equipped kitchen.
5 Bedroom Beautiful Home - Oakville
No reviews

5 Bedroom Beautiful Home

apartment, Milton
This five-bedroom, three-bathroom flat in Milton's central district offers convenient access to local attractions, placing you within easy reach of the Milton Abbey and the Milton Market.
This well-appointed residence accommodates up to ten guests, featuring a kitchen with a fridge, microwave, and dishwasher, alongside air conditioning, a garden, and parking, ensuring a comfortable stay.
South Oakville Bliss Haven: Spacious 5 Bedroom Home With 2 Kitchens And Terrace - Oakville
No reviews

South Oakville Bliss Haven: Spacious 5 Bedroom Home With 2 Kitchens And Terrace

apartment, Toronto
This West Oakville flat is located approximately 32 kilometres from Toronto Pearson International Airport and 36 kilometres from BMO Field, offering a residential setting with straightforward access to city attractions.
This spacious accommodation, ideal for up to 10 guests, features five bedrooms, three bathrooms, two kitchens, air conditioning, free Wi-Fi, and is situated near family-friendly activities and a local mini-market.

Frequently Asked Questions about vacation rentals in Oakville

  • What should a first-time visitor not miss in Oakville?

    Oakville has a lot to offer, but for a first-timer, you shouldn't miss the waterfront. Stroll along the Oakville Harbour, visit the Oakville Museum, and maybe catch a show at the Oakville Centre for the Performing Arts.
  • What are the best Airbnb and vacation rentals in Oakville?

    Waterfront Coach House Loft, The Wine Cellar and Cozy 2 Bedroom Basement Apartment are the most popular Airbnb and vacation rentals in Oakville among travelers.

  • Which neighborhood in Oakville should you consider for a vacation rental?

    For a vacation rental, you might want to consider the Old Oakville neighbourhood. It's charming, with historic buildings and a vibrant atmosphere, and it's close to the waterfront and shops.
  • What are the most popular Airbnbs in Oakville?

    Among the Airbnbs in Oakville, Waterfront Coach House Loft, The Wine Cellar and Cozy 2 Bedroom Basement Apartment are the most popular ones.

  • What are the top family-friendly attractions in Oakville?

    For families, the Oakville Museum is a great place to start. Kids will love the hands-on exhibits, and the museum's location on the waterfront makes it even more appealing. Also, the Oakville Public Library is a great place to visit with children, with a variety of programs and events.
  • What are the best vacation rentals with a pool in Oakville?

  • When is the best time to book a vacation rental in Oakville?

    The best time to book a vacation rental in Oakville depends on your preferences. If you want to experience the summer festivals and outdoor activities, July and August are ideal. However, for a quieter getaway, spring or autumn might be better.
  • What are the best rentals for families and kids in Oakville?

    The best rentals for families and kids in Oakville are Home Away From Home (Basement Apartment), Pathway Suites and Cozy & Beautiful Basement Apartment.

  • What events or festivals should visitors check out in and around Oakville?

    Oakville has a lively events calendar throughout the year. The Oakville Jazz Festival in July is a popular event, and the Oakville Fall Fair in September is a great family-friendly event. You could also check out the Bronte Creek Provincial Park for events.
  • What are the best rentals or Airbnbs with a jacuzzi in Oakville?

    The best vacation rentals or Airbnb with a jacuzzi in Oakville are Pathway Suites, Beautiful Cozy 1 Br Condo Steps To Sq1 and Luxurious1 Br Condo In Downtown Mississauga .

  • What are the best budget-friendly activities in Oakville?

    Oakville has plenty of free and budget-friendly activities. A walk along the waterfront is always enjoyable, and you can explore the many parks and green spaces. You can also visit the Oakville Public Library, which offers free events and programs.
  • What are the best restaurants with local dishes in Oakville?

    For local dishes, try the Oakville Fish Market for fresh seafood, or The Oakville Chop House for a classic Canadian steakhouse experience. For something a bit more casual, The Oakville Brewing Company serves up delicious pub fare.
  • What are the best walking or cycling routes in Oakville?

    The Waterfront Trail is a popular choice for walking and cycling, offering scenic views of Lake Ontario. The Oakville Creek Trail is another great option, winding through the town's natural areas. You can also check out the trails at Bronte Creek Provincial Park.
  • Are there pet-friendly attractions in Oakville?

    Many parks and green spaces in Oakville are pet-friendly, including the Oakville Harbour. You can also find dog-friendly patios at some restaurants and cafes.
  • What are the benefits of choosing a vacation rental in Oakville?

    Vacation rentals offer more space and privacy compared to hotels. They often come with amenities like kitchens and laundry facilities, which can be convenient for families or longer stays. They can also be a more affordable option, especially for larger groups.
  • What are the top sports attractions and facilities in Oakville?

    Oakville has several sports facilities, including the Oakville Soccer Club, the Oakville Tennis Club, and the Oakville Golf Club. The town also hosts a variety of sporting events throughout the year.

Popular destinations

Best Oakville vacation rentals with a balcony

Modern & Spacious 2 Bedrooms+2 Bathrooms Bungalow In Oakville - Oakville
No reviews

Modern & Spacious 2 Bedrooms+2 Bathrooms Bungalow In Oakville

house, Toronto
Accommodation. Your accommodation will be based in Toronto.
Services and facilities: a washing machine, an iron and a kitchen. Enjoy free parking with this accommodation in Toronto!
Modern Luxury Designer Home The Poshest Neighbourhood In Canada - Oakville
No reviews

Modern Luxury Designer Home The Poshest Neighbourhood In Canada

apartment, Toronto
This designer townhouse is situated in West Oakville, offering proximity to Lake Ontario and a 48-64 kilometre drive to Toronto's city centre.
This luxurious four-bedroom, three-bathroom property accommodates up to eight guests and features a private backyard with a swimming pool, a barbecue, and is equipped with air conditioning, high-speed internet, and five parking spaces.
Modern Luxury Home Near Bronte Harbour & Oakville Downtown - Oakville
No reviews

Modern Luxury Home Near Bronte Harbour & Oakville Downtown

house, Toronto
This spacious five-bedroom detached house is situated in Oakville, offering a peaceful setting 37 kilometres from the Mississauga Convention Centre and 42 kilometres from BMO Field, with the marina a mere 720 metres walk away.
The property boasts 19 square metres of floor area, accommodates up to 27 guests, and features a fully equipped kitchen, a fireplace, an indoor play area, a balcony, a garden, private parking, and free WiFi.
Royal Stays Townhome Collection - 3 Bedroom Townhome In Oakville - Oakville
No reviews

Royal Stays Townhome Collection - 3 Bedroom Townhome In Oakville

apartment, Milton
This 3-bedroom townhouse is located in Oakville, just 27 kilometres from Mississauga Convention Centre and Toronto Pearson International Airport, and 37 kilometres from BMO Field and Budweiser Stage. The property enjoys excellent location and cleanliness ratings, with guests consistently praising its comfort and convenience.
The townhouse offers 172 square metres of space, comfortably accommodating up to 6 guests. A fully equipped kitchen, private terrace, air conditioning, free Wi-Fi, satellite TV, and parking are all provided for your enjoyment.

Best Oakville vacation rentals with air conditioning

Stylish 2-bed Oakville Home With Free Parking + Wifi - Oakville
10 1 review

Stylish 2-bed Oakville Home With Free Parking + Wifi

apartment, Milton
This self-contained side unit in Oakville, located 1.5 kilometres from Lake Ontario and 2.1 kilometres from Bronte Creek Provincial Park, offers convenient access to amenities and natural attractions for those visiting Milton. This two-bedroom flat accommodates up to four guests and features a fully equipped kitchen, in-unit laundry, air conditioning, and dedicated parking, with an office area suitable for business travellers.
Sun-kissed 3br Family Home In A Quiet Neighborhood - Oakville
9.9 126 reviews

Sun-kissed 3br Family Home In A Quiet Neighborhood

apartment, Toronto
This spacious home is located in Oakville, a suburb 30 kilometres west of Toronto, and is close to Sheridan College, Walmart, Oakville Place mall, and the lakeshore. The property enjoys excellent user, location, and cleanliness ratings.
The detached house offers 3 bedrooms and 1.5 bathrooms, comfortably accommodating up to 6 guests. The house is fully equipped with a modern kitchen, a large garden, high-speed internet, free parking, and automated check-in and check-out.
Luxury Basement Apartment In Oakville - Oakville
No reviews

Luxury Basement Apartment In Oakville

apartment, Milton
This Oakville apartment, a short 18km drive from Milton, offers easy access to Lake Ontario, Erindale Park, and Joshua Creek Heritage Art Centre.
The one-bedroom, one-bathroom flat sleeps four guests and includes Wi-Fi, air conditioning, and essential toiletries; nearby family attractions include Playdium and Amazing Adventures Playland.
Premium 3br Oakville /Pool, Gym And Parking, Close To All Hwys & Shops - Oakville
No reviews

Premium 3br Oakville /Pool, Gym And Parking, Close To All Hwys & Shops

apartment, Toronto
This three-bedroom flat in Oakville offers convenient access to major motorways and shopping centres such as Square One and Toronto Premium Outlets, with Lake Ontario situated a short distance away.
This residence provides on-site Wi-Fi, air conditioning, a pool, and a gym, along with practical amenities like a clothes dryer and towels, making it suitable for travellers seeking a serviced apartment in the Toronto area.
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